


Oh dear brother!

by Anonymous



Category: Supernatural
Genre: Alpha John Winchester, Anal Beads, Barebacking, Begging, Blow Jobs, Crying, Dubious Consent, First Time, Humiliation, M/M, Marking, Non-Consensual Spanking, Overstimulation, Painful Sex, Prostate Milking, Punishment, Rape/Non-con Elements, Riding Crops, Rough Sex, Size Difference, Size Kink, Spanking, Unrealistic Sex, copious amount of cum
Language: English
Status: Completed
Published: 2019-10-09
Updated: 2019-10-11
Packaged: 2020-11-28 09:30:54
Rating: Mature
Warnings: Rape/Non-Con
Chapters: 2
Words: 6,075
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20964314
Author URL: https://archiveofourown.org/
Summary: Dean is not pleased to see his little brother's neck littered with hickies.





	1. Chapter 1

**Summary for the Chapter:**

> SUMMARY: Dean is not pleased to see his little brother's neck littered with hickies.

**Chapter 1**

Dean huffed and slammed the door shut. He fumbled with his pockets and shoved the key into the doorknob. Stupid officer who decided to interrupt him when Lily or whatever her name was about to tell him something important.

Dean knows it’s something important. He could just feel it in his gut.

“Dean?”

His tense shoulders loosen. _ Sam _. His baby brother Sam was home from whatever he was doing in the library. He was usually never home early enough to see his little brother. A whiff of bacon invaded Dean’s smell. Sam was being a perfect little wife, cooking Dean some food to come home to.

“I’m home Sam.” Dean nearly bit off his tongue when Sam appeared with bruises on his neck. Dean has had enough one night stands to know what exactly those bruises were, and it certainly wasn’t from pain. He stormed over to Sam, discarding his jacket on the way, his skin heating up from rage. Calloused fingers gripped Sam’s chin, tilting his head up and down. Whoever did this was clearly smug about it, since the hickies were placed so high up that Sam wouldn’t be able to cover it without makeup. “What’s this?”

Sam blinked his eyes, cheeks blossoming as red as his plump lips. Dean nearly melted on the spot. His cute baby brother was blushing. Despite growing a good inch or so taller than Dean, Sam was still so adorable. Dean snapped out of his thoughts, anger coiling in his stomach. His baby brother was blushing because some fucker touched what wasn’t theirs. Dean twitched, his thumb pressing against a dark purple spot just beneath Sam’s chin.

He growled. Sam pushed Dean’s hands off.

“Nothing. I was just having fun.”

Dean cocked one eyebrow, he could feel his anger boiling over, “_ Fun _? Who said you can have fun, Sammy?”

Sam snorted, copying Dean’s actions. “I’m an adult, Dean. I can do whatever I want.”

“Oh yeah?”

“Dean don’t make a big deal out of this. You have plenty of fun every night.”

Dean grabbed Sam’s wrist, squeezing a little too hard. His eyes darkening when Sam’s colour turned paler. His eyes bore into his little brother, who wasn’t so little anymore. “I don’t do it for fun. Granted, I do one-night stands, but it has a purpose, Sammy.”

“It’s Sam now. Not Sammy. I don’t see the difference between your one night stand and mine’s. You know what, why don’t you go cool yourself down. Come back inside if you’re ready to talk like a mature adult.”

Dean dangerously narrows his eyes. His grip on Sam’s wrist tightened, watching in fascination when the skin grew a little pink. Sam winched, trying to wrench back his wrist.

“Dean let go. You’re hurting me—_ Dean!” _

Dean ignored his little brother, dragging him into their shared bedroom. The motel was decent for 25 bucks a night, but it might have had to do with the fact that this was in the middle of nowhere. That also meant no one was going to hear them and the owner had retired to his own house for the night. 

Dean shoved Sam on their bed, Sam grunted and sprawl on their bed, he stared at Dean in disbelief.

Sam glared at him while nursing his pink aching wrist. Dean smirked, his head brimming with ecstasy when he noticed a blooming mark on Sam’s wrist. He was sure that there was going to be a mark there tomorrow morning.

“Sammy, my dear little Sammy.” Sam shivered, fear creeping up, and Dean forcefully parted Sam’s legs until he was sitting in between them. He brushed the back of his knuckles on Sam’s cheeks. Feeling Sam’s cheeks flare up, probably due to embarrassment. “You just don’t know who you belong to, do you?”

Sam furrowed his brows and pushing lightly at Dean’s chest. Dean was acting too weird today and he definitely wasn’t liking it one bit. He bit back a groan when one of Dean’s hands landed on his thighs. “Dean, I’m not in the mood for jokes. Move it.”

Dean clicked his tongue, not budging from his position. Dean pushed Sam down, hitting his head on the headboard in the process. Sam groaned in pain, opening his eyes back up to see Dean hovering over him.

“No.” Dean growled out. Sam paled, blood running cold. Was this even his brother anymore? “_You. Are. Mine. Sam_.”

Sam clicked his tongue, getting ready to get back up when Dean pressed a hand on his chest, and leaned down to kiss him. Sam slammed his fist on Dean’s chest, earning a painful grunt. He wasn’t expecting Dean to slam his full weight, knocking the air out of his chest. He gasped and Dean returned for a second kiss, shoving his fat tongue into Sam’s hot mouth. Sam whined, debating between biting his brother’s tongue off and slamming his brother unconscious. His mind reeling as his mouth began to get engulfed by his brother’s fat tongue. He turned his head to the side, hazel eyes blinking the tears away. 

“What the fuck, Dean?! What the hell is your problem?!”

Dean smirked, licking his red lips. Sam unconsciously did the same and flinch at the rawness of his lips. Sam jerked his knees, successfully hitting Dean in the stomach, he underestimated his brother’s reflex time, Dean had slammed Sam’s head onto the headboard. Sam felt the room rolling, bile raising to his throat. 

Dean clicked his tongue. “Sammy, be good. I don’t want to hurt you.”

_ Too late _. Sam wants to say. But he’s more focused on the fact that his brother nearly threw him into a coma. He barely even notices Dean tying his hands onto the headboard, taking his clothes off and tucking a pillow behind his back. Fully exposing him to Dean. He returns back to reality when Dean’s eyes are boring holes into his body. His naked body. His cheeks lit up, refusing to meet Dean’s gaze. 

“You want to know what my problem is, Sammy?” Dean peppers little kisses all over Sam’s naked body. Sam squirms, trying to jerk his inner thigh away when Dean drops a kiss too close to his dick. Too close for his liking. He honestly couldn’t understand what Dean’s problem with him was. 

“If this is about the one-night stand, then I won’t do it again!” 

Dean laughs, leaning too closely to Sam’s chest for his comfort. He kisses Sam’s chest and Sam doesn’t know what Dean is up to but he knows he isn’t going to enjoy it. “Now, now, it’s too late for that, Sammy. You let someone else touch you.”

“W, what? Y, you, fu—!” A scream rips out of Sam’s throat, his eyesight blurring up. Sam refuses to believe the intense pain he felt. He stares at Dean’s wild eyes, his pink tongue darting out to lap at the blood collecting around Sam’s chest. Sam whimpered, his pecs burnt so bad but the feeling of Dean sucking his nipple felt good. It overpowered the feeling of pain. 

Sam squirmed his hips, Dean was swallowing his nipple, alternating between chewing on his nipple and giving a gentle suck like a newborn baby.Dean kissed Sam’s right nipple and then moved over to the other nipple. Sam’s face paled, watching a smirk stretch over Dean’s face. Dean opened his mouth wide, nipping lightly around the fragile skin. 

Sam shook his head, whimpering, “No, please, Dean, it _ hurts— _” Another scream ripped out of Sam’s throat. He sobbed openly. His chest hurt so bad and Dean didn’t seem like he was going to stop any time soon. 

“So good for me, baby.” Dean lapped at blood oozing out from the bite mark he left on Sam’s left pec. He sucked Sam’s left nipple until Sam was whimpering underneath him. He moved to give Sam a chaste kiss. Sam eagerly returned the kiss, licking Dean’s lips, Sam's head brimming with heat, pain and arousal. 

Dean shifted his hips around, moving it until his clothed cock met with Sam’s naked slowly growing cock. Sam moaned, hips shuddering at the friction of fabric of Dean’s jeans. Dean played and explored Sam’s mouth, making sure not a single spot was left untouched by his tongue. Sam turned his head, breaking their sloppy kiss, his cheeks lighting up at the obscene sound it made when he parted his lips from Dean's. He was losing all the strength to fight Dean off

His older brother shifted uncomfortably, he could see Dean’s erection looking ready to burst out of his pants. Sam bit back a moan when Dean gave a particularly sharp thrust. “De, Dean, please. We can’t do this. We’re brothers.”

Dean ignored him in favour of discarding his clothes. Sam swallowed nervously, he hadn’t seen his brother’s cock in years but it definitely was bigger than the last time he remembers. There was no way his cock would fit in his ass. Dean leaned down, kissing Sam’s inner thighs, pinching it when Sam attempted to close his thighs together. Shame filled Sam’s face, his eyes tearing up. He shivered when Dean blew on his cock. “Dean, please, don’t do this!” 

Dean flick his eyes up; Sam’s teary eyes were also a good look on him. He gave his younger brother a naughty grin, opened his mouth and latched onto the head of Sam’s leaking cock. He sucked the tip hard, and pinned down Sam’s frantically wild legs. 

Sam cried softly, his hips rutting towards the roof of Dean’s mouth. It just felt so good to get a blowjob. After being bitten on his pecs, this blowjob was godsend. He whimpered when Dean refused to take his cock down his throat. 

“Dean, please!”

Dean removed his lips from Sam’s cock, teasingly licking the leaking slit, “Please what, Sammy?”

Sam’s cheeks burnt. He didn’t want to beg his brother. He didn’t even want this in the first place but he just wanted to chase after his pleasure. He wanted to burn the memory of the painful bite on his chest. 

“Please, Dean! I need to cum!”

Dean beamed, “As you wish.” Dean swallowed Sam’s cock, taking it down to the hilt. His nose hitting the base of pubic hair. He hummed, throat constricting and vibrating onto Sam’s cock. Sam squirmed, toes curling. He could feel himself reaching his climax. His thighs closed around Dean’s head, pushing his cock down Dean’s throat, and he barely remembers what happened. 

He knows Dean kissed him, giving him his own cum. It’s salty and disguising but he swallows it down anyways. 

Dean looks pleased and started to pump his limp cock. Sam let out a broken cry. He couldn’t get it up anymore. Not so soon. Dean picked up a little bottle next to their night stand. Sam shivered at the cold lube dripping from his cock to his ass. Dean made an appreciative sound. Then he ran a finger near Sam’s hole. 

Sam quivered, closing his legs only to be stopped by Dean’s hands. “I, I have never done this before, Dean!”

“That makes me so happy, Sammy. I will make sure that you love this.” Dean purred out, rubbing some more lube on his fingers.

Dean kissed his brother’s inner thigh, a rush of excitement. _God_. His baby brother always knew what excited him. Sam forced himself to relax, knowing that Dean was planning to go all the way. He obediently opened his legs, feeling a little wanton by the position and tries to ignore the pressure on his ass. Dean watches intently as his finger pushes inside of Sam’s ass. 

A sob racked through Sam’s body. It was so uncomfortable to have a finger up his ass, but Dean didn’t care. Dean’s finger gently pumped in and out. Then he grew bored of it. He began to push in another. Then another.

Sam’s body arched, trying to accommodate the rush of three fingers—it was too much, and too little prep time. He could feel the incredible stretch his ass was going through. Sam mewled softly, burying his face behind his tied hands. 

Sam squirmed, trying to adjust his position but Dean had abnormally large fingers. He could feel his ass’s failed attempt at trying to accommodate the sudden intrusion and he just knew that taking a cock today would split him open. He needed time but he knew just how impatient Dean could be. 

“D, Dean! It hurts.”

Dean silenced him with another kiss, his tongue roofing Sam’s mouth. Sam moaned when Dean’s fingers thrust inside at a fast pace. Dean jerked his fingers in random directions until he finally found that little bundle of nerves. Sam choked on a cry, eventually it became a string of messy incoherent words as Dean continued to assault the bundle. Dean watched in awe as his brother’s cock leaked like an open facet. His fingers continued to rub the nerves until Sam came all over his stomach, Sam's angry cock spurting on his stomach.

Dean eyes darken. Sam was so gorgeous and obedient. He was such a good little slut. 

After a moment, Dean pulled out his fingers and poured the lube over his hands and pumped his cock a little before lining the head of his cock to Sam’s ass. He felt Sam’s hands pushing at his stomach.

“Dean, n, no, p, ple—”

Dean pushed his hips a little, moaning when the head of his cock caught on Sam’s puckered rim. It was so sexy seeing the head of his cock pushing inside of his baby brother. He didn’t know how hot having anal sex was until now. Dean grunted and pushed a little more and Sam’s face paled.

It was so good. Dean couldn’t stop his hips from stuttering which forced his cock a little deeper into Sam. He wanted to take this slow. He wanted Sam to get used to it, but Sam’s ass was being a little needy slut and sucking his cock inside the warm hole. Eventually, Dean lost all restraint and buried the rest of his cock inside. Sam’s hands scrambled to grab onto Dean’s wrist at his hips.

“Dean…_please_…go slower…” Sam cried out, body shaking from the sudden intrusion, he had given up all hopes that Dean would stop. The least he could do was make sure that his brother didn’t rip anything. Anal sex was painful and needed careful preparation. 

Dean stilled, he wanted to let Sam get used to the feeling but the hot walls clenching down on him made his hips rut lightly but he tried his best not to move. He was still Sam’s big brother. He had to let Sam get used to the feeling of his cock. Dean gritted his teeth. Sam was so good to him. So tight and so warm. Like Sam’s ass was made just for his cock.

He licked the shell of Sam’s ears. Hotly whispering, “You’re being such a good boy for me, Sammy. Can you feel me? Can you feel your ass making some room for my cock?”

Sam’s cock twitch, he was so dirty for getting turned on by his brother’s dirty talk. He shifted a little which caused his brother’s cock to rub against his abused prostate. He whimpered, nails raking against his brother’s back. Sam gritted his teeth, he really tried his best not to cry out in pain but it really hurts. Asses weren’t meant to take cocks even if Dean had prepared him well.

That was what a pussy was for.

Sam’s eyes began to tear up even more on the incredible stretch his ass was going through. Dean wasn’t even that small by standards but his bastard brother just shoved his cock inside. Sam gasp when Dean began to pull up until only the head of his cock was inside Sam’s ass.

“D, Dean, go slowly…please”

Dean cooed, his little brother was encouraging him to go on with this. His cute little brother loved having his cock inside his ass. Dean’s eyes flick down to watch Sam’s ass tightly clench onto the head of his cock. The rim around his ass was fluttering, torn between sucking him back in and pushing him out. 

God, it was so sexy, and hot. Dean kiss Sam on the lips, and Sam obediently responded. Sam was just so sexy and good for him. So slutty. He held Sam’s hips, fingers digging and thrust down in one go causing Sam’s back to arch and his cock to leak some more. 

Dean chuckled. His baby brother was made to take a cock. Made to take his cock.

Then Dean repeated it again, and again, setting a steady pace. Eyes concentrated on his cock slipping in and out and engorging with more and more blood until Dean could feel himself getting closer and closer to his own release. 

“P, please, Dean!” His brother’s broken cries broke Dean out of his trance. His brother was pumping his cock. Dean laughed, and Sam grew more embarrassed. Dean slapped Sam's hands away and gripped his brother’s cock pumping the angry red cock. And before long, Sam’s body tighten up and his toes curled, mouth opening as his cock squirted out thin pale watery semen. Dean gritted his teeth and continued to pump his hips._ In and Out. In and Out._ He was closed, the walls of Sam's ass clenching down on him. His hands tighten around Sam’s hips, his steady rhythm became erratic. A moan escaped Dean’s lips and slammed his hips one last time making sure to spurt his semen as deep as he could into Sam’s body. Dean moaned softly, kissing his brother when Sam clenched around his cumming cock. 

Sam whined, squirming at the foreign hot liquid flooding his ass. His ass automatically clenched down on Dean's oversensitive cock, the older boy hissing in his ears. 

“Fuck…” Dean groaned out, pulling his cock out to see the mess he made out of Sam's ass. His mouth watered, watching Sam's hole bubble up with his thick semen. If Sam was a girl, Dean was sure Sam would have been pregnant. Dean slipped his thumb into the irritated red hole, “Such a good slut, Sammy. Going to milk my cock like a good slut, right Sammy?”

Sam sobbed and shaking his head. He was so tired and his eyes were flickering between blacking out or trying to focus on his surroundings. Dean planted little kisses around Sam’s neck, biting over the hickies. He gently mouthed at Sam’s lips, licking and was granted permission. Sam was finally accepting Dean and didn’t have the energy to fight him anymore. Dean leaned back. Basking in his prized possession, he slipped in beside Sam, and spooned his little brother.

He was tired. Tired from failing to get information from that Lily girl. Tired from coming home to a disobedient Sammy.

_Disobedient_.

He needed to remind himself that Sammy needed to be punished for being such a bad boy. Dean’s mind raced. Spanking his little brother was a good idea or maybe he could make Sammy wear a cock ring for a whole month or maybe he could milk Sammy until he begged to be fucked.

All three ideas sounded good. His cock twitched in agreement.

Dean brushed Sam's hair back, his thighs pushing Sam's legs apart to feel his warm cum slipping out of Sam's ass, “You were such a good boy for me, Sammy. Taking my cock so well. We’ll have to do this again tomorrow night, be ready for your punishment. I don’t appreciate your disobedience today.”

Sam curled up into a ball, whimpering. He felt so filthy and the thought that he might go through this again made him dread tomorrow. Sam could feel intense fear creeping up on him. He could ignore today but his brother was planning to continue this tomorrow. His ass hurt like a gunshot, and he was positively sure that he was going to be limping tomorrow. 

Dean wrapped his arms around his baby brother. Slowly lullabying to sleep with his baby brother nice and safe in his arms. 

Sam couldn't sleep that night. 

**Notes for the Chapter:**

> A/N: this was written in an hour. No beta read but hopefully y’all love it!


	2. Chapter 2

**Summary for the Chapter:**

> SUMMARY: Dean punishes his baby brother after yesterday's event

**Chapter 2**

Dean wakes up earlier than Sam. For once, he didn’t sleep a wink, adrenaline running through his veins. He was just so excited for the sun to come out. He had ditched the motel as soon as he saw the small peak of dawn. He tucked Sam's body back into their shared blanket, kissing the boy lightly before he headed out. Sam was in for a real treat today.

Dean had to be real careful. There were a lot of things he knew and with that came pretty much illegally obtained information. Dean couldn't control the smirk from appearing on his face as he approached a small shop. He made eye contact with the woman, both staring intently. She didn't speak. He didn't either. She stepped aside and he gave her an acknowledged nod. 

Some people may even consider it sinful but who really gives a damn. Dean left the shop, bidding the girl a low goodbye as he made his way out of the shop with two large suspicious black bags. Tossing a credit card he had stolen from Matthew Collins. 

///….///

Sam wakes up with a dull aching pain on his backside. His chest is throbbing and looked like they weren't going to heal with how deep Dean had bitten his pecs. There was a chance that Dean might have done it on purpose. To leave a permanent mark on his body. Sam twitched, sitting up on the bed, his hazel eyes widening when he sees his reflection in the mirror above the dresser. His whole body is littered with dark wounded bites and bruises from yesterday’s events. Sam's not even sure if his previous partner's hickies were even there anymore.

He wrapped a hand around the large bite mark on his chest, winching lightly when a sharp pain shoot through his chest. It tingled. Dean didn’t hold back at all. 

“Careful there, Sammy.” Sam snapped his head up, seeing Dean all freshen up after a shower. He was only wearing a towel around his waist. Sam didn't even know Dean was showering. He didn't even hear the water rushing. Sam’s cheeks lit up, his eyes trailing at Dean's exquisite body structure. He chastise himself, his older brother had forcefully fucked him yesterday and yet here he was, oogling at his brother's body and acting like some horny teenager in love. “Go shower, Sammy. I got a surprise for you.”

His face paled, seeing the predatory smirk on Dean's face. Sam can’t stop the dreadful feeling he gets in his guts but he doesn’t argue with Dean. He could but he was afraid to argue. Sam slipped his weak legs off of the bed, struggling every step of the way and limped to the bathroom. He barely managed to hold back from swearing at his brother when Dean gave him a generous slap on the ass on his way past Dean.

Sam shuts the door and sets the water on near boiling hot. He can see his skin glow red and takes his time cleaning himself. Everything hurts. He felt sore down there but Dean didn't care. Sam stands on his shakily legs, and bends over the tub, Sam's sure that Dean was going to fuck him today as well. He can hear his shakily breath echo too loudly, his legs trembling from the aftermath of yesterday's event but he snakes his fingers between his ass and squirms uncomfortably until he manages to push in two fingers inside his puffy asshole. He curls his fingers, and pushes out the cum his brother had left there.

His cheeks flared up in shame. His damn brother didn’t even clean him. 

Sam curls his two fingers, his asshole protesting. The rim of his ass felt raw and sore. He takes a shaky breath and probes a third finger in. He barely manages to contain his gasp when his nails brushes against his prostate. Sam knows it's his prostate because he's had a prostate exam before. He hits his forehead against the tiles. His mind reeled back to what Dean had said—_I have a surprise for you_. Sam gulps. Dean’s not the type of person to do surprises. 

_ Oh. _

Fuck...The event from yesterday runs through his mind. Dean must have bought something for his punishment. A shiver ran down Sam’s back. He couldn’t. _Not now_. His body wouldn’t be able to handle it. Sam stared at the towel. He could escape with his towel. People might call the cops on him but it was at least better than getting punished by Dean. Sam finished rinsing up and brings his ears on the door, quietly listening to what’s happening outside. 

He can hear the television and there’s a strong smell of something. _Food_. His mind supplied helpfully. Food that Dean was cooking. He would be too occupied with cooking to even notice Sam. He opened the door as quietly as a creaky door could open. He slipped out of the room, grabbing one of Dean’s discarded shirts and shorts. He would have to go commando for today. 

There was no time to waste. 

Sam tiptoed out of their shared bedroom, making his large body as small as possible as he gently walked down the stairs, hiding between the walls. He grimaced when the floor beneath him creaked. 

“Where are you going?” 

Sam froze. Refusing to turn his head around.

Dean clicked his tongue, turning Sam around. Dean was still holding a spatula. But his eyes darken, lips pulled into a tight line. _He was unhappy._ Sam whimpered nervously, his hands unconsciously rubbing the back of his neck.

“Just going out for a breath of fresh air.”

Dean didn't look impress, “Nonsense. I’ll open the window. Come, we have to eat. We have a long day in front of us.”

Sam was so tempted to bolt out of the room but he was still limping and sore from yesterday. There was no way he could out run Dean, not when Dean had his impala. As soon as Dean turned around, Sam heatedly glared at his brother and took a seat in front of Dean, allowing his older brother to feed him. Apparently the damn room only had one set of spoon and fork. Sam obediently opened his mouth, letting his brother baby him. 

Dean beamed, feeding his baby brother while occasionally taking bites for himself.

Sam wanted to hurl. His mind was running on miles. He needed to figure out a way to get out of here. His brother was just out of his mind. Something must have hit his brother. Some evil force. Sam was sure of it. Preoccupied with his thoughts, Sam didn’t notice Dean leave the room until Dean came back with two large black bags. 

Sam yelped when his chair spun around and Dean was sitting in between his legs. 

“What the hell, Dean?!” 

Dean gave him a sultry smirk, batting his eyes innocently while spreading his legs wider. Dean took out a weird looking contraption, he was working on Sam’s zipper. 

“Stop, Dean!” Sam brushed Dean’s hands off. “I, I’m sore from yesterday. Can’t we do this tomorrow?”

Dean clicked his tongue, still pulling out Sam’s limp cock out of his shorts. Sam groaned, this was going nowhere. He could either go along with Dean and hope it ended early or continue fighting with him and risk the chances his ‘punishment’ gets worse. Sam’s not even sure why he was getting punished in the first place. Dean took Sam’s limp cock, and pushed the flesh into the contraption. Sam hissed at the restriction he was feeling. “What the fuck, Dean?! A fucking cockcage? Where did you even get that?”

Dean winked at his brother, kissing the precum beads collecting at Sam's slit. “_Secret_.”

Sam shivered. That shouldn’t be hot at all. Not after his brother forcefully had sex with him yesterday. _Fuck_. Sam was so messed up. 

“Come on, get up and bend on the table. I will give you twenty spanks for yesterday.”

Sam didn’t move, instead, he intensified his glare at Dean, crossing his arms stubbornly. Dean chuckled and manhandled him into the position, if Sam wasn't so sore, he would have busted Dean's balls. Brothers or not. A whimper escaped his lips when his bruised chest slammed on the dining table too hard. Dean pinned his brother, pushing Sam's shoulder down and ripped the shorts off. Sam heard his brother make an appreciative grunt of approval and rubbed his ass cheeks with warm hands.

"Stay."

Sam did. He could hear Dean shuffling with the black bag. Sam shuddered, feeling something foreign running down his ass crack. He nearly bit his lips off when something thin landed square on his ass—_Fuck, it hurts. _

“Count for me, Sammy.” Dean squeezed his ass. Sam knew that he was going to be in so much pain tomorrow. 

"What the fuck was that?" He barely manages to grunt out. "That wasn't a spanking--"

Dean clicked his tongue. "I said count for me. Let's start again." 

_“1.”_ Sam managed to utter out. Air rushing out of his lungs faster than he expected. Whatever his brother was using to 'spank' him hurt. _It hurt a lot_. His ass felt like it was on fire. Sam didn’t want this. His throat tickled, eyes blurring. But he refused to cry out. Another sharp pain landed directly on his ass. 

_ “2.”_ Sam choked out. It was a fucking riding crop in his brother’s hand. Dean cruelly grinned. He was putting in a lot of effort into his blows. His cock twitched seeing the mark his crop was leaving on Sam’s pale ass. _God, it looked really good_. _Sammy just looked so good_. By the fifteenth hit, Sam began to openly sobbed. It was just _too_ much and it was _too_ painful. 

Some of Dean's whipping landed on his asshole and his ass was still _fucking_ raw and sore from yesterday. Sam sobbed when Dean spread his ass cheeks and whipped him right at his asshole. 

Dean shushed him, walking around to meet eyes with Sam's. His erection tenting his pants once he sees the tears dripping down Sam's face. He gently caress Sam's cheeks, wiping the tears away and kissed him gently. Parting a little to whisper, “It’s alright, Sammy. Just a little more.”

Sam shook his head, clenching Dean's hands, “No more, D, Dean. I, it _hurts_. I'll die—”

“Are you telling me what to do, Sammy?” Dean gently slapped Sam's cheeks. His breath hitched when Sam trembled, quickly shaking his head. Dean muttered praises into Sam's ears. Walking around to look at Sam's ass. His prized possession. Sam's ass was now a deep bruising colour, Dean's hardwork was starting to show through. "I believe I asked you a question, Sammy."

“N, no.”

“Then, will you be a good boy and take the last 4?” 

Sam sobbed but nodded his head. He couldn't take it anymore. Even though 4 seemed so little. He was sure his ass was going to be on fire. He was so hot, he swore he could faint from all this pain. Even getting attacked by a demon was better. Sam couldn't contain his pained cries when Dean swung the last five. Sam was sure that Dean had put his best effort in the last five.

Dean dropped his crop whip. Eyes zoning in onthe red ass cheeks. He licked his lips, and touched the busted red ass, Sam jerking away from his touch.

“Now, your punishment isn’t over yet.” Sam shook his head. _No more_. Just how much more could Dean want from him. “I got this vibrating dildo.”

Dean pours the cold lube all over his heated ass and it takes all of Sam’s strength not to jerk away when Dean rubs the vibrator dildo on his puffy rim. “So gorgeous Sam. Have you seen your ass?”

Sam hasn't. But, he knows for sure that it's fucking _wrecked_ after yesterday and today's ordeal. He's also sure that his puffy asshole isn't even an asshole anymore. Sam stiffens, forcing himself to relax as Dean gently pushes the dildo inside Sam’s hole. Dean gets an inch inside, he plays with Sam's asshole for bit. Liking the way Sam's puffy rim are clinging to the head of the fake cock in his hands. 

Sam gasped as Dean pushes another inch inside. His grip on the table tightened,_ it really hurts. It hurts so much._ His ass was fucked raw yesterday and Dean still wanted to continue. He could have at least given Sam a day to rest and recover. 

Dean gently thrusts half of the vibrating dildo in and then plays with the toy. Eyes soaking in how Sam's asshole refused to let go of the toy. His cock was ready to burst out of his pants. Dean's afraid he would have to be satisfied with Sam's blowjob.

He purred in delight when he finally sinks in the rest of the dildo, watching Sam's body shake, his throaty moans filling up the room. He flipped Sam over, finally flicking Sam's limp caged cock. A smirk spread on Dean's face, his free hand playing with Sam’s limp cock trying to get erect but was restrained by the cockcage. 

“So good for me, Sammy.”

Sam wanted to curse at him. _Tell him how crazy he was being_. But his mind float away. The sharp jerks at his prostate makes him forget everything. Dean roughly shoves the dildo one last time causing Sam to shudder, his hips rutting at the dining table. 

“Come on, put your pants on, we have a case to do.”

Dean pulls Sam up to sit, he watches in glee when Sam's mouth gape open knowing that the dildo somehow pushes in deeper. Sam stands on his shaky legs.

He should have bolted when he had the chance. He should have risked it. At the very least, he tried, he could have been successful if he had tried.

Sam whimpered, allowing Dean to pull up his pants, and fix his clothes. Dean escorts Sam to his impala with a hand around Sam's waist. Sam sits in the shotgun as usual, and angles his ass so that he's not putting any weight on the dildo.

But of course, Dean has other things in mind. He drives the impala roughly than usual and keeps an eye out for any potholes just so he can drive over them and jostle the whole impala just to see Sam's horrified face. Dean can't stop the giddiness he feels when he sees Sam biting his lips and trying his hardest to keep his weight off his ass.

///….///

Dean plays with Sam's hair, his baby brother was knocked out. Tuckered out. Their case had ran the whole day and Sam tried his hardest to ignore the dildo in his ass. Dean had enormous fun, alternating between roughly picking the worst roads to drive in to purposely slapping Sam's ass every chance he got. It took Dean fifteen hours of keeping Sam locked up in a cockcage and dildo before his baby brother broke.

Sam kneeled as soon as Dean shut the door to their motel and begged Dean to fuck him. Sam’s cock had been an angry purple, so upset at not being able to release and who was Dean to refuse when his baby brother was begging so prettily like he was made to be a slut. A personal cumslut for Dean. So he did. Dean fucked Sam good. He had fucked Sam multiple times. He had fucked Sam unconscious. He would have continued but he would have to continue tomorrow. He still had other toys to test out.

Dean embraced his brother a little closer, his brother squirmed and tucked his face into Dean’s neck. Dean’s fingers rubbed at Sam's entrance, delighted to feel the warm wet cum seeping out of Sam's asshole. He'd have to invest in a plug to make sure Sam didn't waste any of his seeds. His fingers felt around the puffy rim. Sam's ass must be in so much pain right now.

Sam whined softly in his sleep.

Dean kissed his brother's brows, but first, Dean would have to go get medicine from the pharmacy tomorrow morning. 

**Notes for the Chapter:**

> This is for you Amber!  
I was initially going to released another pairing but decided to continue with Dean x Sam, where Dean punishes Sam after yesterday's event. In case, anyone is wondering, this is connected to chapter 2.


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